Multiple relay configuration based on sender address with sendmail

One of the needs that came up was to be able to use separate relay configurations based on the sender email address, using sendmail. The problem is that sendmail is missing support for most parts of that sentence.

At the end the solution involved a combination of sendmail, smarttable, procmail and msmtp

The idea is the following:

  • Use smarttable to implement sender based rules
  • Use the procmail mailer support to use procmail to deliver the emails
  • Use procmailrc to pipe messages to msmtp
  • Use msmtp to relay via external hosts

Sender based rules

In order to be able to have sender-based rules I used smarttable.m4 from here.

Download the smarttable.m4 and (assuming sendmail config is under /etc/mail) place it under /etc/mail/m4/. Normally it should be placed along the rest of the sendmail features (/usr/share/sendmail/cf/features) but I don’t like polluting system dirs. Then use the following config in

dnl Change the _CF_DIR for a bit to load the feature from /etc/mail/m4
dnl then change it back
define(`_CF_DIR_OLD', _CF_DIR_)dnl
define(`_CF_DIR_', `/etc/mail/m4/')dnl
dnl This has to be a hash. I.e. not text.
FEATURE(`smarttable',`hash -o /etc/mail/smarttable')dnl
define(`_CF_DIR_', _CF_DIR_OLD)dnl

Then configure smarttable (/etc/mail/smarttable) like this:    procmail:/etc/mail/persource/

You can add as many lines as you like, one for each sender. See smarttable’s web page for more information on the supported sender formats. Dont’ forget to generate the hashed version (smarttable.db)

Procmail config

Configure sendmail for procmail mailer like this:

define(`PROCMAIL_MAILER_ARGS', `procmail -Y -t -m $h $f $u')dnl

You have to override the default procmail parameters in order to add the -t switch. This way delivery errors will be interpreted as softfails, otherwise mails will be rejected on the first failure.

Create /etc/mail/persource and put the procmail configs in there (nice and tidy). In this example create /etc/mail/persources/ as follows:

|/usr/bin/msmtp -C /etc/mail/persource/ -a -t

The ‘w’ flag is essential in order to feed failures back to sendmail.

Msmtp config

Create the msmtp config file (/etc/mail/persource/ as follows:

syslog          on
# logfile /tmp/

password        xxx
auth            on
tls             on
tls_trust_file  /etc/ssl/certs/ca-certificates.crt

Your mileage may vary. They above is good for gmail accounts on a debian system.


And that’s it. Sending an email as will cause sendmail to use smarttable. This will match the sender and use procmail with our config to deliver the email. Procmail will pipe the email to msmtp which will send the email via google’s email servers.

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